The Caring & Creative Leader

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 “Leadership isn't about being in charge. It's about taking care of those in your charge.”

—Simon Sinek

Leadership isn’t just about strategy or authority. It’s about people. It's about creating space for others to thrive. In a world that’s changing fast, we need leaders who can think creatively, act empathetically, and evolve constantly.

One of my foundational beliefs is that good leadership is a creative act, a daily practice of making decisions, shaping culture, and designing experiences that help others grow. And like any creative process, it’s messy, imperfect, and always in progress.

So how do you become a more caring and creative leader?

🎨 The Creative Leader

Creativity isn’t reserved for artists. Leaders use creativity every time they:

  • Reframe a problem in a new way

  • Tell a compelling story to inspire change

  • Design a better workflow or meeting structure

  • Navigate conflict with empathy and imagination

In his book Originals, Adam Grant puts it this way: creative thinkers don’t just challenge the status quo—they rebuild it. They ask “What if?” instead of “What is?” And they invite others to contribute their own ideas, voices, and talents.

Creative leaders don’t need all the answers.  They need the curiosity to ask better questions!

🧪 Learning Through Failure

Failure is not the opposite of leadership; it’s the raw material of growth.

When you create something—whether it's a project, a team, or a vision, you will mess up. That’s not a flaw. That’s a feature.  I like to approach leadership and experience design like a scientist testing a hypothesis.  Try something and if it doesn't work, figure out why and try again with this new information.

Leaders who can learn publicly, take ownership, and bounce forward model something powerful:

  • That failure is a teacher, not a verdict.

  • That vulnerability is a leadership strength.

  • That improvement isn’t just possible—it’s expected.

Creative leaders embrace iterative thinking. Just like a game designer tests and refines a prototype, or a writer revises a draft, great leaders are willing to try, fail, and improve—over and over.  The Irish writer Samuel Beckett put it best: 

"Ever tried. Ever failed. No matter. Try again. Fail again. Fail better."

🔁 Continuous Improvement: A Leadership Mindset

The best leaders are never done growing. They build cultures of feedback, reflection, and reinvention. That means:

  • Listening deeply, not just to metrics but to people

  • Adjusting processes when they’re not working

  • Experimenting boldly, even when success isn’t guaranteed

  • Celebrating small wins, because they’re the seeds of incremental transformation

This isn’t perfectionism; it’s progress. Leadership is a living process, not a fixed position.

💡 Leading Like a Creator

Want to lead like a creator? Here’s what it looks like in practice:

  • Be playful in your problem-solving. Try weird ideas. See what sticks.

  • Create psychological safety for your team to experiment and fail forward.

  • View leadership as a design challenge, not a control mechanism.

  • Reflect often. Improve constantly. Stay curious.

And most importantly, lead with care.

🛠️ Try This

Host a “Lessons Learned” circle:
At the end of a project, invite your team to share one thing that worked, one thing that didn’t, and one bold idea they’d like to try next time. Normalize reflection and improvement—and participate honestly yourself.  The trick is to make sure it doesn't turn into a finger pointing session.  The goal is to identify the "what" not the "who." If there are people problems or skill issues that need to be addresses, they will become clear through identifying the issues.  Those can be addressed with the individuals rather than in a group.

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